Build your own CTO Playbook at www.theCTOplaybook.com — the leadership platform built for the full CTO journey. Coaching, podcast, and community to help you lead with clarity, confidence, and strategic impact.

Your most powerful decision engine isn’t your data, your dashboards, or your AI, it’s your gut.

There is a topic that most technical leaders quietly wrestle with: gut instinct. Not as mysticism. Not as guesswork. But as a real decision-making tool for modern CTO leadership.

This episode is all about why your instincts are often your experience compressed into a feeling, when you should trust that signal, and when you absolutely shouldn’t. You’ll hear real coaching stories from seasoned CTOs navigating technical leadership, roadmap trade-offs, scaling engineering teams, and high-stakes calls where the data wasn’t enough.



We’ll talk about how engineering leadership changes when you treat instinct like a cached function, fast, powerful, but sometimes stale, and how to validate it without killing its speed. This episode is for startup and enterprise technology leaders who want sharper judgment, fewer regret-filled postmortems, and more confidence saying, “Something about this feels off, and here’s why.”

If you’ve ever ignored your gut and paid for it later, or trusted it blindly and been burned, this conversation will give you a practical way forward. It’s about building better instincts, not just better systems.

You’ll Learn:

[00:00] Introduction

[01:02] Why seasoned CTOs sense problems before they can explain them

[03:18] How ignoring gut signals leads to overcommitment and roadmap failure

[05:07] What gut instinct really is — experience compressed into a signal

[07:26] When instinct fails in new or emotionally charged situations

[09:41] How to spot where your instincts are strong, weak, or distorted

[12:12] Treating instinct like a cached function — fast but fallible

[16:34] Using gut instinct as a warning without turning it into dogma

[20:18] How data can validate instinct without slowing decisions

[24:47] A playbook for sharpening instinct under pressure

Find more from Adam on LinkedIn and YouTube, and check out Adam's CTO coaching company here.

Build your own CTO Playbook at www.theCTOplaybook.com — the leadership platform built for the full CTO journey. Coaching, podcast, and community to help you lead with clarity, confidence, and strategic impact.

Most CTOs fail not because of bad decisions, but because they stop asking why.



In this episode, I sit down with Massimo Belloni, Head of Machine Learning and Data Science at Docplanner, to discuss what real technical leadership looks like when the answers aren’t obvious.

We dig into bold CTO leadership, why engineering leadership is mostly about people, and how curiosity in leadership builds trust faster than authority ever will. Massimo shares hard-earned lessons from leading ML teams across industries, and why the job isn’t about being the smartest person in the room, but creating conditions where teams thrive.

If you’re navigating CTO mindset shifts, managing high-performing engineering teams, or feeling the quiet weight of imposter syndrome in tech leadership, this conversation will land. We talk about invisible leadership work, asking better questions, and why progress only makes sense in hindsight.

Iif you’re leading through complexity and change, this episode is your reminder: certainty isn’t the goal, clarity is.

You’ll Learn:

[00:00] Introduction

[02:14] How Massimo realized leadership is about people, not technical mastery

[05:48] Why trying to be the smartest person in the room backfires

[09:37] What changes when you lead systems you don’t fully understand

[13:22] Why most leadership problems aren’t actually technical

[17:54] How asking why builds trust faster than giving answers

[22:41] Why strong teams come from safety, not fearlessness

[27:36] How invisible leadership work compounds over time

[33:18] The question Massimo uses to measure leadership progress

[38:47] Why leadership only makes sense in hindsight

Resources Mentioned:

The CTO Playbook episode on The Key Relationship That Drives Startup Growth with Steven Renwick | Spotify or Apple

Steve Jobs Stanford Commencement Speech | YouTube

You can connect with Massimo on LinkedIn and learn more about his work on his substack here.

Find more from Adam on LinkedIn and YouTube, and check out Adam's CTO coaching company here.

Build your own CTO Playbook at www.theCTOplaybook.com — the leadership platform built for the full CTO journey. Coaching, podcast, and community to help you lead with clarity, confidence, and strategic impact.

The real reason invoices don’t get paid has nothing to do with accounting.



Late payments aren’t just annoying, they quietly drain focus, energy, and leadership bandwidth. In this episode I sit down with entrepreneur Maximiliaan van Kuyk to discuss why trust in business payments is breaking down, and what CTOs can do about it.

Drawing on years of experience across startups, agencies, and global markets, Maximiliaan explains why accounts receivable is no longer just a finance function, but a leadership and systems problem. They explore how late invoice payments persist not because people are malicious, but because incentives are misaligned, and accountability is invisible.

You’ll hear why consistency beats confrontation, how social accountability in business can outperform legal threats, and why CTOs should care deeply about cash flow management even if they never touch invoicing.

If you’ve ever felt the quiet frustration of waiting to get paid, or watched payment delays impact runway, morale, or growth, this conversation will reshape how you think about trust systems, AI in accounts receivable, and the future of getting paid on time.

You’ll Learn:

[00:00] Introduction

[02:18] Why getting paid is really a trust problem, not a money problem

[06:41] How chasing payments drains founders emotionally and why it usually lands leadership

[10:52] What happens when small businesses become accidental lenders, and why the system works against them

[15:37] Why consistent follow-ups beat confrontation and legal threats when recovering unpaid invoices

[21:04] Why late payments persist even with contracts and how incentives shape behavior

[27:56] How social accountability changes payment behavior faster than reminders or credit scores

[34:48] Why reputation only works when it’s visible, and what hidden payment history enables

[41:22] Why CTOs need to understand cash flow risk even if they never touch invoicing

[48:09] How tracking payment behavior could reshape trust, partnerships, and who gets hired

You can connect with Maximiliaan on Instagram or find his work on his website here.

Find more from Adam on LinkedIn and YouTube, and check out Adam's CTO coaching company here.